Perry’s personal assistant, Kenneth Iwasama, pleads guilty to shoot the star an ovedrdose of Ketamin

Matthew Perry’s tragic final moments involved a disturbing request for ketamine, a drug to which he had become addicted.

According to court documents obtained by NBC News, the 54-year-old “Friends” star, who was found dead in his hot tub last October from the acute effects of ketamine, instructed his live-in assistant Kenneth Iwamasa to “shoot me up with a big one” during his last hours.

Iwamasa, 59, has pleaded guilty to conspiracy to distribute ketamine causing death. He admitted to repeatedly injecting Perry with the drug, despite lacking medical training, and continued to do so on the day Perry died. On October 28, Iwamasa reportedly administered ketamine to Perry three times—at 8:30 a.m., 12:45 p.m., and approximately 40 minutes later—according to details in his plea agreement.

The documents reveal that Perry asked Iwamasa to prepare the jacuzzi and requested another dose of ketamine, leading to Iwamasa leaving the house only to return and find Perry face down in the hot tub.

Perry, known for his struggles with substance abuse, had been undergoing supervised ketamine infusion therapy for anxiety and depression. However, a toxicology report released in December determined that the fatal dose of ketamine could not have come from his prescribed therapy, as the last session had occurred a week and a half before his death. Ketamine has a half-life of no more than four hours.

Earlier this week, a source close to Perry revealed to Us Weekly that his friends and family were “blindsided” and “saddened” by the news of Iwamasa’s involvement. The source noted that Perry’s sobriety was unstable and that multiple people were involved in his care.

The U.S. Attorney’s Office for the Central District of California announced charges against Iwamasa and four others: Dr. Salvador Plasencia, Dr. Mark Chavez, drug dealer Jasveen Sangha (known as “The Ketamine Queen of Los Angeles”), and director-producer Erik Fleming, who acted as a broker for Sangha.

According to Iwamasa’s plea agreement, Perry paid at least $55,000 to Dr. Plasencia in the month before his death and approximately $12,000 to Fleming for two drug deals with Sangha, including one shortly before his death that resulted in the ketamine that killed Perry.

Plasencia, who allegedly guided Iwamasa on drug administration, pleaded not guilty to conspiracy to distribute ketamine. Dr. Chavez has agreed to plead guilty to the same charge and faces up to 10 years in federal prison. Fleming pleaded guilty to both conspiracy to distribute ketamine and distribution resulting in death. Sangha, linked to a prior fatal overdose, faces nine counts related to Perry’s death and has pleaded not guilty.